Massachusetts Road Trips

In the heart of New England, Massachusetts is a perfect place to start any road trip. Boston is a fun town filled with historical significance, great food, professional sports and things to do. From there, great destinations in numerous states are merely a few hours away. Take a ride with Enterprise Rent-A-Car and start your journey from Massachusetts today!

Massachusetts Road Trips

Historic Drive from Philadelphia to Boston

Filled with American history around every turn, the drive from Philadelphia to Boston is fun, intriguing, and offers plenty of things to see and do. Pick up a rental vehicle and enjoy this scenic road trip.

Hop in the car and drive from New York to Boston. Discover interesting stops along short drive from the Big Apple to Beantown.

Explore the Northeastern U.S. on this road trip from Boston to Bar Harbor, where you'll find a unique mix of history and awesome scenery along the way.

Discover some of the best scenery the East coast has to offer on a road trip from Boston to Cape Cod. Book an Enterprise rental car to visit all the best stops along the way!

Explore Bristol, New Haven and more as you drive from Boston to New York City using this weekend trip itinerary.

Looking to go from New York City to Nantucket? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.

Looking to go from New York City to Cape Cod? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.

Road Trip to Maple Sugar Shacks in New England

From New Orleans to the Northeast, one foodie sets out to explore the sweet beyond.

Artsy Provincetown Offers an Inclusive Getaway

Everyone is welcome in this Massachusetts beach town.

Rockport, Massachusetts, is a Relaxing, Seaside Getaway

The quaint town offers a bounty of seafood, a scenic shoreline and even a house made of paper.

Yoga Retreats of the Northeast

Legendary resorts ensure a relaxing journey.

Massachusetts Trips

Plan your next road trip, weekend getaway or personal challenge.

Cape Cod Drive Reinforces Benefits of Slow Travel

Cape Cod’s laidback vibe is apparent when you steer your Enterprise rental car along historic Massachusetts State Route 6A, a road less traveled that offers quality time. Relax on the National Seashore, explore charming towns and enjoy fresh oysters at every stop.

Following the Berkshire Cheese Trail

Head to Northeast dairy country for some of America’s finest cheeses.

People are discovering the origins of their food.

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Looking for more road trip ideas? Check out our Road Trip Planner and choose your next journey!

Road Trip Ideas

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Massachusetts Road Trips